


Can't Get You (Out Of My Head)

by orphan_account, WithMyTeeth (Ylith)



Category: Teen Wolf (TV)
Genre: Alternate Universe - Fraternity, Anal Fingering, Anal Play, Anal Sex, Blow Jobs, Bottom Stiles Stilinski, Dom/sub Undertones, External Prostate Stimulation, Feminization, Fraternities & Sororities, Gay Panic, Hazing, Homophobic Language, Humiliation, Jealousy, Just the Tip, Lack of Communication, Lingerie, Loss of Erection, M/M, Mildly Dubious Consent, Penis Size, Photography, Prostate Massage, Prostate Milking, Puppy Play, Rough Sex, Size Difference, Size Kink, Small Penis, Stiles Stilinski has a Small Dick, Top Jackson Whittemore, Under-negotiated Kink, Watersports, face fucking, sub space
Language: English
Status: In-Progress
Published: 2016-03-27
Updated: 2017-02-26
Packaged: 2018-05-29 12:51:20
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 7
Words: 18,852
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6375499
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/orphan_account, https://archiveofourown.org/users/Ylith/pseuds/WithMyTeeth
Summary: <blockquote class="userstuff">
              <p>It's Hell Week Bitches. </p><p>Jackson was expecting just another year of hazing desperate freshers for his frat. The time however, something about one of the boys has him paying /special/ attention to this kid's hazing. </p><p>A love story about: humiliation, feelings, denial & blow jobs.</p>
            </blockquote>





	1. Night 1.

**Notes for the Chapter:**

> I (AlternativeName) somehow managed to convince Ylith (WithMyTeeth) to write another story with me.  
> (I know, I'm so lucky.)
> 
> We went for frats, because Jackson is so obviously a douchebag frat boy. We also went with Stiles having a MASSIVE humiliation kink. 
> 
> We've already written about 5 nights of this, and are hoping to finish off the last few soon. I thought we should upload some now to give us the motivation to finish this beast off. 
> 
> Notes on writing: we just switched in and out, each of us taking on different chunks at different times, hopefully it has come together fluidly.

"All right maggots, you heard Pledge Master Mahealani. Get your fucking clothes off and show your brothers the sorry excuses you call your dicks!"

 

Jackson strutted up and down the line, smirk tugging at his mouth as he surveyed the reddened cheeks and discreet glances the pledges gave each other. It always stated like this, fresh meat who weren't sure if the orders were legit, but were too scared to risk their place at the prestigious Fraternity to question it.

 

They were still fully clothed and already Jackson could see a few of their faces pinking, see their eyes fall to the floor as they struggled with the desire to please and the fear of exposing themselves, the fear of being deemed "inadequate" by a group they desperately wanted to belong to.

Jackson revelled in it, felt excitement bloom in him as he saw the first of them begin to crack. He zeroed in on the guy, a good looking kid with tan skin and a crooked jaw. "Something wrong, Pledge?" Jackson asked, spitting the word out.

 

"No brother," the boy said, his hands still clasped behind his head in the position they had previously been ordered into. "I just..."

 

Jackson glanced up to Aiden, the other boy casting him a dark grin which served to only egg Jackson on. "You just what?" Jackson asked, brows raised in mock sympathy. "You just felt like you'd come out here, take some other guy's place and waste our time with your bullshit?"

 

Tan Kid's eyes widened, head shaking emphatically. "No, I just...I mean I didn't think we'd have to-"

 

Jackson rolled his eyes. "You don't think, Pledge. This is Hell Week, you do as we say, or you get the fuck out, understand? There's the door, if you're not up for it, then go ahead."

 

Tan Kid's mouth hung open, looked like he was still parsing Jackson's words. In a move lacking any and all subtlety, he tilted his head towards the boy next to him, a pale little thing with moles flecked across his jaw. "Stiles, you coming?"

 

Jackson zeroed in on the "Stiles" kid, eyes narrowed hawkishly while he waited for a response. He was practically tingling with anticipation when he saw Stiles dare to glance up at him, immediately dropping his gaze, his cheeks staining a splotchy pink.

 

"...'Stiles' is that a name?" Jackson sneered, hoping for a reaction. The boys eyes kept glancing up between Jackson - who was now standing very close to him - and his little tan friend, who was trying to steal him away.

 

"Yes, Stiles.... Sir. I mean, fuck, brother." The boy said in a breathy whisper, his complexion getting ruddier by the minute. Jackson was in his fucking element.

 

: "Oh, you can call me sir if you want _brother_. But how about it STILES, are you gonna’ run away with your tail between your legs, or are you going to give your dick some air?"

 

Lots of the pledges were watching the interaction, Jackson could see that most of them were grateful that his attention wasn't on them. The boy glanced at his friend again - who was twitching his head violently towards the exit - before screwing his eyes shut and began undoing his belt buckle.

 

"Ding - ding - ding, we have a winner. That's one space of 8 filled for pledges, whoever gets their ass out first just might win one of the other 7!" Jackson called.

 

He would admit that he might have jumped the gun a /little/ for automatically giving the boy a space, but the prospect rubbing in that little 'sir' slip up all week was positively delicious. The tan boy has huffed, and started taking off his own clothes (muttering to himself) and Jackson started patrolling again up and down the aisle

 

The tan boy huffed his disdain and began to remove his own clothes. Jackson patrolled up and down the line, jumping viciously at one of the pledges who had visibly bad acne down his back, all the way down to his ass. "Jesus christ, you fucking troll, you should have probably given that some air long before tonight" - it was satisfying when the boy began to cry, he hadn't gotten that sort of reaction out of someone since he was in highschool.

 

His brothers were also harassing the pledges, taunting them, and snatching their clothes away when they hit the floor. Finally, when all of the boys' were standing awkwardly in the nude, Jackson filled them in on the next part of the plan. "Aiden, go get the buckets of ice."

 

Jackson walked down the line while Aiden went for the buckets, arms crossed over his chest until the muscles bulged. He puffed with pride as he surveyed their bodies, confident in the fact that his was far superior to any offered. Tan Boy was pretty cut, but didn't have Jackson's bulk. He had a decent dick though, much to Jackson's chagrin. He instead stopped by the boy to the left, raised his fingers to press against the underside of the guy's peck. "Bitch tits?" he said with a condescending head tilt. "May be a bit too saggy for Alpha Phi...what do you think, Brothers?"

 

Jackson kept his eyes locked on the guy's face as he spoke, watched the shame well there as the guy fought to not make any outward reaction. Jackson could see him squirm though, saw the little twitch in his fingers when he resisted the urge to make a fist. He just stood and took it, impotent.

 

A few of the pledges held their hands over their crotches, tried to shy away from the scrutiny, and Jackson made quick work of them. One of them caved, a guy with glasses, a skinny body, and chubby cheeks. The brothers all laughed as he stooped to collect his clothes, one of them nudged his bare ass with a foot until he fell on his face, but he kept his hands firmly planted over his crotch.

 

Jackson found himself back in front of the skinny kid, Stiles. Stiles' posture was rigid, but his head bowed in supplication, arms straight down at his sides with hands curled in fists twitchy with anticipation. Jackson pursed his lips, eyes wandering down the length of that gangly body onto to zero in on the soft prick between his thighs. God, the kid had a cute dick. Soft and pink with tight little balls nestled close to his body behind it. Jackson wanted to cup it, wanted to run his thumb down the length of it until the kid was gasping and crying from the effort to keep from coming.

 

Instead he stopped before him, brows climbing his forehead as he swirled his finger in the kid's face. "Turn around pledge, show me that ass."

 

The flush crept down Stiles' face into his throat, his lower lip caught between his teeth as he bit back some comment. He wasn't graceful, but turned as told, head hanging low. He yelped when Jackson slapped him hard on his bare ass, the flesh smarting immediately from the heat of it. "Look at that ass, Brothers!" Jackson yelled in delight. "You a fag, pledge? Cause it looks to me like you were made to take a dick... you're not fucking anyone with that pathetic little baby cock."

 

Jackson practically vibrated with excitement when Stiles turned back around, eager to see the humiliation shining in his eyes, see his face go pale from the urge to run. When Stiles turned though, he was pink and he did look ashamed, but his sweet little prick was also plumped up with blood.

 

The fucker was getting hard, kept getting hard even when Jackson scoffed at him.

 

"What the fuck!"

 

Jackson broke from his little haze when Tan Boy...Scott, whatever...stepped forward, actually shielding Stiles from Jackson's view.

 

Aiden chose that moment to come back with the ice, but Jackson had to deal with Scott first. The kid had some real stones to stand up to him while bare ass naked and in a room of upperclassmen, definitely not brains but balls for sure. Not that Jackson would give him the satisfaction of acknowledging this in front of the other brothers and Pledges. Hell no.

 

"What the hell do you think you're doing Pledge? Get back in line." Jackson jabbed a finger towards the open space Scott's empty head was supposed to be.

 

Scott shook his head, not budging. "This is fucked up," he said. "Hell week or not, you shouldn't talk to people that way."

 

Jackson could practically feel the silence from his brothers behind it. They were all spineless pussies, the lot of them. One little pledge pipes up and suddenly none of them can nut up and take charge?

 

"You don't like it? There's the door," Jackson reminded him again. "You get out of line one more time and we'll toss your ass out of it."

 

Scott looked back to Stiles, likely assuming his friend would have had enough and be ready to go with him. Jackson half expected him to finally throw in the towel too, but when Scott stood back and gently asked Stiles to come with him, the kid just stood there. Stiles' face was red as a beet, but his hands remained at his sides, his head bowed submissively, his prick still just as swollen.

 

"Stiles, come on."

 

Stiles just shook his head, much to Scott's dismay and Jackson's utter delight.

 

"Looks like he's happy where he is, Pledge" Jackson practically purred. "Last chance. In... or out?"

 

Scott's jaw clenched in anger, but he backed up into the line again. Jackson would bet his Porsche that he was only staying to keep an eye on his friend, but he couldn't care less. He only had eyes for Stiles.

 

Order restored, Aiden began dumping the ice on the naked pledges. They howled and sputtered under the frigid onslaught, but instead of reveling in their discomfort, Jackson kept his eyes trained on Stiles. Watched every twitch and shift as he waited his turn. Jackson stepped in closer, right up in his space, and he cast a sharp look towards Scott, daring him to make any sort of objection. Scott looked ready to blow a gasket, but remained still and silent.

 

Jackson pursed his lips, pointedly looking down at Stiles' crotch. "I don't know, Pledge...can your dick even get smaller? Do you think the ice will make any difference?"

 

Stiles shuddered, dick twitching at the words, but he didn't speak. Let Aiden dump the ice over his head and shoulders with little more than a flinch. Jackson watched water trickle down his face and drip onto his smooth chest, glide down his flat belly...

 

Jackson forced himself to look away, want settling warm and heavy in the pit of his stomach. He was getting hard, and he had to get away from this kid before anyone else noticed.

 

Jackson rarely liked to give into temptation, prided himself on his ability to overcome any obstacle, best any challenge he'd set for himself. He'd never let desire get the best of him, never let himself want another guy, yet all the same there he was. This awkward, geeky kid with an upturned impish nose made him want to get to his knees, rub his face in that soft belly. He wanted this boy alone, in his bed with that ridiculous plump mouth open and gasping. Wanted to see those eyes wide, his thighs trembling as he held back the urge to cum. Wanted to hear his own name fall from that pretty mouth, desperate and needy, like only Jackson could give him what he needed.

 

Jackson sneered openly at how weak he sounded in his fantasies. A streak of bitterness against the boy tainted the image, like the little fag has infected him - that must be it, right? Caught up in a torrid mixture of arousal and malice, when the other frat brothers began picking pledges to be their 'slave' for the week, Jackson grabbed one of the remaining buckets of ice water and threw it in the boy's face. "Fucking take that, you piece of shit. I call this little bitch - I can count on you fucking running from here before the week's out - just you see!" A flash of emotion passed through the boy's face - he wasn't entirely sure if it was shame - but when the pledges were all forced to walk naked around the block before being allowed to retrieve the clothes, he saw Stiles' eyes repeated glance at him, flushed with curiosity.

 

**Notes for the Chapter:**

> Spoilers/tags: I added dubious consent as Stiles is kinda' Jackson's pledge here, so there probably is some abuse of authority. But at any time, Stiles can just bow out. And tbh, it's pretty obvious he doesn't want to.
> 
> Please comment and kudos. We love praise. Almost as much as Stiles loves being humiliated.


	2. Night 2

**Summary for the Chapter:**

> Jackson finally gets some time to himself with the pledge.
> 
> Check notes at the end for warnings.

The pledges had all been woken up at 6am (only 3 hours after they were allowed to go to bed) and forced to run laps around the quad that morning. After that they'd been given menial house jobs to do all day, before being sent off with the task to grab something to eat and do all the brother's laundry. Jackson knew they weren't allowed to actually force the boy's to faint with hunger or exhaustion, so there was no strict time for 'slaves' to return to the brother that had picked them, but there was a strong recommendation that they don't be too late. "Who knows, the last pledge back might get kicked out!" Danny had warned them.

Jackson had been lounging on his bed, watching youtube videos and browsing clothes to buy online when he spotted Stiles and his tan friend through the window, walking back towards the house. They were too far away for him to know exactly what they were saying, but the larger boy looked quite incensed and heated up. Stiles, alternatively had an infectious grin on his face, answering whatever his friend was saying with dramatic hand gestures. Jackson caught himself eyeing the boy's neck as the figure had thrown his head back in unfiltered mirth, prompting him to jump off the bed and begin to drag things haphazardly out of draws and cupboard and onto the floor.

Once the room was sufficiently disorganised, Jackson resumed his position lounging on the bed, plugging in his headphones and clicking play on a video about how some London rapper had made his most recent music video.

This meant that when Stiles finally came through the door (the boy knocked, opened the door a jar, before just hovering in the hallway waiting for Jackson's attention) it was easy for him to completely ignore the pledge. He was waiting for the minute that Stiles' began to sigh, fidget, or maybe even try to leave - so he could snap at him - but Stiles stood there with a surreal level of stillness (especially when compared to the moments Jackson had managed to snatch looking at the boy when Stiles was around his friends, where the teen seemed positively vibrate) that by the time Jackson's 15 minute long video had ended, he'd had no reason to reprimand the boy. "Not to worry" Jackson thought to himself, "he'll squirm soon enough."

When Jackson finally swiped his eyes up to look at the boy, the pledge twitch slightly, as if the attention had snapped him back to the present. "You're late." Jackson snarled, even though this was quite plainly untrue. Stiles' chewed at his lip, before defaulting back to that breathy voice from before, "I'm sorry."

"Is that anyway to address your superiors, pledge?" Jackson snapped

"No-no.. No Brother, sorry Brother."

"Tsk. You're losing your edge pledge... "

Jackson was quite excited about what he had planned, but he didn't want Stiles' to know that. Cool indifference was the best way to play this off, Jackson loved making people feel small and uncertain. That only worked if they thought that they were below your interest.

"I want you to tidy this shit up, start over there by the cupboard, I want everything put away. You fuck up any of my clothes, pledge, and I'll fuck you up. You got that?"

"Yes, Brother... ...Sir."

Jackson sent him a wicked grin, one that clashed horridly with the utterly cruel look in his eyes. "Well then, get the fuck on with it."

He put his headphones back in and went about ignoring the boy again. It was difficult, he had the strong urge to watch the pledge like a hawk: the boy still had this electric stillness to him still, like he'd been put on standby, and was ready to snap at any moment. Jackson was also eagerly awaiting even the slightest of errors the boy was to make.

Half an hour in, and Stiles dropped one of Jackson's textbooks he didn't realise was in the bottom of a bag. It was enough. "What the fuck, you piece of shit! How fucking retarded are you!" Jackson roared, leaping up from the bed, and crowding in against the slighter boy.

"I'm... I'm sorry brother. It was an accident."

"Of course it fucking was, you obviously fucking incapable."

Stiles' looked on high alert, colour had appeared slightly high on his cheeks.... But something about the boy seemed to relish Jackson's attention.

Jackson, if it wasn't clear in his daily actions, was inherently a bully. His favourite position was to make those around him feel small; and if he didn't achieve that with his words, he was very happy to gain that respect with his fists.

Stiles' failing to cower sufficiently in front of him had his blood pumping slightly, the urge to just slap the boy across the face was strong. Properly put the little shit in its place. Unfortunately, it's probably go against the hazing guidelines...

Thankfully, Jackson had a backup plan.

"I think you need a lesson in understanding your place pledge.... Strip."

Unlike the night before, Stiles' did not hesitate before moving. His hands had a nervous thrum to them, but in all, he followed the orders perfectly.

It felt as if the room was getting hotter with every inch of flesh that Stiles' revealed to Jackson, and the older boy had to take a few steps backwards so as to not reach out and grab at the pale pectoral muscles - lacking in tone but defined nonetheless - now open to him. He played it off as fetching the two more interesting items for the evening.

From a draw beneath his bed Jackson removed a standard polaroid camera and a pair of lacy pink girls underwear, he laid them out on the bed beside him, and allowed himself to glance back at the pledge. Stiles was staring at the items, his eyes the size of dinner plates, his hands gently twitching at his sides.

"You know what those are pledge?" Jackson ask, pointing at the underwear.

"Yes... Women's underwear Brother."

"Wrong! They are _your_ underwear. Unless you're a little girl, pledge. Tell me, are you a little girl, pledge?"

Stiles did not seem to know how to answer this, his eyes darted from Jackson to the underwear a few times. Before finally easing out a...

"I don't know... I am if you want me to be brother."

The words were like a smack to the face for Jackson, warm arousal pooled in Jackson's belly at the skittish yet flirtatious line.

"You little piece of shit. Put your fucking underwear on like the little bitch you are." Jackson ground out. His own eyes hunting down the movements as the boy darted towards the underwear, stepped into them, and drew them up his thighs.

The boy, who had looked a tiny bit smug a moment before, was turning a rather apt pink now that he had to navigate tucking his cock into the confining - but rather translucent - laced garment.

 "Look at you, finally wearing the right clothes." Jackson spat, he picked up the polaroid camera and snapped a photo of Stiles awkwardly trying to lay the seam over his trapped cock.

"What a pretty fucking girl you make. Your little cock all dressed up. Does it feel good to be wearing your underwear pledge?"

Stiles looked like he was practically vibrating now, the boy nodded his head, a gentle "Yes brother" escaping between his lips.

"Turn around for me."

Jackson had to muffle his gasp of air as he saw the little round globes of flesh peak out the bottom of the underwear.

"Bend down for me... More.... Even more..." Jackson snapped another photo.,

  
"I'm not surprised a little girl like you would have such a pretty butt. Need to work it hard like a little slut I bet. That baby cock isn't going to get wet any other way..." Jackson was rubbing his erection through his jeans mindlessly as he berated Stiles "...a fag bitch like you has to spend all his time on his knees."

The urge to see Stiles' face again was palpable for Jackson, forcing himself to move his hand away from his crotch, he barked another order.

"Turn around, get on your knees."

The expression of Stiles' face was delicious, screwed up in a mixture of embarrassment and misery, juxtaposed to the quite clearly plumped erection straining against the dainty underwear.

Jackson whistled. "Look at you, you want it so bad. Your little clit is soaking." Stiles swallowed a whine at Jackson's words, and in that moment Jackson just _needed_ to hear more.

"Touch yourself. No-no. Keep them on. Rub your baby cock through them. Yeah, just like that, pinch the tip of your clit. Show all the boys how pretty you are."

Jackson snapped another few photos, it was torture not to touch himself right then and there, to smear his prick up against the sodden material, he had to keep some form of evidence for latter.

"Open your mouth." Jackson bit out, his own eyes darting up to the pouty pink lips that had been sealed shut seconds before. With a pop they separated, and along with it, the pitiful moans of Stiles' embarrassed enjoyment littered the room.

"I bet you want a fat cock in there. A bet you're hungry to prove yourself useful. Can you feel it in your mouth, can you feel it fucking against your tongue."

Stiles lost it at that, his hips snapped forward awkwardly, trying to increase the pressure of his hand rubbing against his cock through the underwear, and within seconds strips of white creamy cum pulsed out of over his hand and erection.

Jackson snapped three photos as quickly as he could. Desperate to capture the moment on film.

They were both silent for a few minutes, Stiles' staccato breaths the only sound in the room. Jackson berating himself for all the urgent thoughts of "Just fuck the boy's mouth" running through his head.

"Get up, and keep cleaning." Jackson finally bit out.

"Wh-what?" Stiles' stuttered back.

"I said get up. Keep those things on. And clean this room like the little pledge slave you are."

Stiles eyes darted over him a few times, his eyes daring to glance down to Jackson's erection once, before he stood and - wobbling like a skittish colt - returned to where he was last cleaning.

With his mind busy with warring thoughts between gratification and denial, Jackson shoved his earphone buds back in his ears and continued browsing the internet. An hour later when he could hear noise in the hallway where other frat members had obviously deemed the evening’s Hell Week activities over, he bit out a, “Get out of my room then, pledge.” Forcing himself not to watch as Stiles hurriedly changed out of his sticky underwear and shuffled into his regular clothes.

It was only later that he realised the boy must have taken the underwear with him. 

**Notes for the Chapter:**

> Warnings:
> 
> Jackson is in a position of authority over Stiles, and thus him ordering Stiles to do stuff that is sexual in nature is super dodgey. He also doesn't check that Stiles is ok with things, before introducing it. Like taking photographs, and the use of femization.  
> As always Stiles is completely free to leave if he wishes to, and quite clearly enjoys/wants to stay in their set up.  
> Jackson quite clearly has some conflicting feelings at the end.  
> \----
> 
> THANK YOU FOR READING. Once again, we thrive from your feedback, so any comments/kudos are utterly appreciated (:


	3. Night 3

**Notes for the Chapter:**

> Remember when I said this is a love story about blow jobs?  
> I really wasn't lying.
> 
> There's no new warnings compared to other chapters. It's just as messy, and porny, and screwed up as before (:

It was a relatively quiet night at the frat house.  A home game meant most of the guys were out either on the field or cheering the team on, or at least using the game as an excuse to get drunk.  Jackson would have gone, usually he went to all the games, but he wasn’t feeling in the right mood that night.  Didn’t want to be around so many people.  

 

He’d been feeling that way a lot, recently.  

 

He lay on the couch in the basement, set before the house TV.  He was watching a rerun of some trashy reality show with his feet propped up on the coffee table.  He couldn’t remember the last time the house had been this quiet.  Loathe as he was to waste such an opportunity, Jackson found himself with his phone out, texting Stiles.

 

-get here now pledge-

 

Jackson had made it his business to know that Stiles was living in the dorms a quick five minutes walk into campus.  Well, five minutes if he hustled, which Jackson assumed he would do.  The pledges were still in full “slave mode”, had to do whatever the brothers asked of them upon command.  Some brothers texted their assigned pledge at four AM, made them go for a jog or fetch something a brother requested.  Few went to the intimate lengths Jackson had with Stiles, though.

 

Jackson felt himself chub up a bit at the memory of the day before, watching Stiles rub himself through his underwear, watching him cum, the confusion on Stiles’ face when Jackson had told him to go back to cleaning.  He wondered if Stiles had told anyone, if he’d figured out yet that some of the things Jackson had done was going above and beyond the usual pledge rituals.  

 

He adjusted himself in his pants, trying to think about anything but Stiles’ lush pink mouth, his curve of his sweet little cock in those panties.  He didn’t want to get too excited too soon, wanted to save his energy for when his little pledge was under his thumb.  Wanted to drag it out, make Stiles flush red with humiliation, see how far Stiles would let him take it, if he’d ever actually tell Jackson no.  

 

Stiles was over in record time, the haste betraying the meager attempt at irritation which furrowed his brows.  “What do you want?” he asked, tone sharp.

 

Jackson quirked a brow.  “Sir,” he reminded, venom gone sugary sweet.

 

Stiles shifted his stance, arms wrapped defensively around his middle.  “Sir,” he spit out.  

 

“I’m thirsty,” Jackson said, face stone in its seriousness.  “Go get me a drink.”

 

Stiles gaped at him, pouty mouth slack and Bambi lashes batting as he sputtered in indignation.  “You seriously asked me over here to get you some water.”

 

“A Vodka Cranberry, actually,” Jackson corrected, leaning against the couch with his arms spread out along the back.  

 

It was a mixture of gratifying and exciting to see Stiles bring a little more bite in his attitude with him. Partially because it meant that Jackson had something to beat out of him, but also because it meant that Stiles had more to him than merely being a stuttering kid. “The more pride they think they have, the further they’ve got to fall,” Jackson mused, nodding his head towards the makeshift drinks bar the frat had implemented.

 

Stiles squinted at the collection of drinks and mixtures, going to take a step towards it before swivelling his eyes back to Jackson. “And that’s all you want… A drink?”

 

“For now.” Jackson answered, his expression all smiles and mild natured generosity, as if he was doing Stiles a favour.

 

The boy, obviously not as stupid as he looked, did not appear to trust him, but made his was over all the same.

 

“A Vodka Cranberry is just vodka in cranberry juice… Right?”

“Stiles, Stiles, Stiles - you’re going to start ruining my good mood if you don’t start addressing me properly.” Veiled threats and mock-concern drenching his voice, Jackson positively glowed at Stiles’ minuscule flinch at his words.

 

“How do you want your drink, brother?”

 

“One part vodka, three part cranberry, lots of ice.”

 

Jackson watched Stiles leave the room, he watched how his jeans clung to his ass as he walked.  Jackson ran the tip of his tongue against his top lip subconsciously, momentarily considering following, but he liked the idea of Stiles waiting on him.  Instead he sprawled back against the couch, sighing with self satisfaction.  

 

Stiles returned in a moment, only one glass in his hands.  Jackson took a sip, furrowed his brows when he eyed Stiles up and down.  “Where’s your uniform, pledge?”

 

Stiles looked down at himself, long fingers brushing along the front of his hoodie.  “What uniform?  I mean...what uniform, Brother?”

 

Jackson’s chest heaved with a heavy sigh, like Stiles was just one big inconvenience.  “The uniform I gave you the other day, pledge.  Your panties.”

 

Stiles blanched, swallowing hard as he parsed whether Jackson was being serious.  

 

“From now on, I want you to wear your uniform when you come serve me,” Jackson said, slow and drawn out as though Stiles needed it.  “For the rest of the week.”

 

“But...what about the other-”

 

Jackson scoffed.  “The other pledges have already seen you’ve got a baby dick, pledge, no need to be modest now.”  Jackson didn’t even blink, not wanting to miss even a second of the other boy’s pinking cheeks.  Stiles looked down at the ground, nodding mutely in agreement.  Jackson had him strip down to his underwear, smirking in delight at Stiles’ small white briefs.  Jackson didn’t think he’d owned a pair himself since he was eight, if he ever did to begin with.  The jokes practically wrote themselves.  

 

Jackson lifted his foot from coffee table and indicated Stiles to sit down.  “I had a long day walking the quad between classes,” he said.  “Why don’t you rub my feet for a while, pledge.”

 

Stiles sat awkwardly on the low table, took the foot Jackson practically thrust into his lap in his hands and began pressing his thumb into the arch.  He kept his eyes on the task at hand, but Jackson kept his gaze fixed on Stiles’ face, watched every twitch and tick as he egged him on.  

 

“You’ve actually got nice lips,” Jackson said casually, almost to himself.  “Dick sucking lips, really.  Maybe I’ll have Lydia from Sigma Delta Chi bring over some lipgloss, have her paint your mouth up pretty.  What do you think about that, pledge?”

 

Stiles very pointedly did not look up, but his cheeks flushed darker, the color creeping down into his neck.  

 

“You’re not really brother material... no offense,” Jackson winked lewdly when Stiles chanced a glance up at him, loved the little worried furrow of the other boy’s thick brows.  “Maybe I’ll just keep you as the house bitch.  You’d like that wouldn’t you.”

 

Stiles shook his head, but Jackson could see how worked up he was getting, noticed the little bulge in his briefs where he was beginning to plump up.  He wanted to touch that mound, roll Stiles’ balls between his fingers until he whimpered.

 

“Yeah, I think that’d go down real well with the brothers. We could all pitch in to get you your little panties, have you wearing different colour every day.”

 

“Did you mean that all the other brothers were going to see me like this?”

 

“Tch-tch-tch. Is that any way to talk to your superiors, pledge?” Jackson sighed, his casual words contrasting the vicious swat down his heel did onto Stiles’ dick.

 

The boy hissed at the pain, and quickly moved to pick up Jackson’s foot again.

 

“Brother! Sir, I just meant…”

 

“Are you scared that everyone will see what a little bitch you are?”

 

Stiles nodded his head a little, his neck a splotchy red color, and his lips pinched in obvious uncomfort. The bulge in his underwear however just pressed more obviously against his little white briefs. 

 

Jackson wanted to change things up a little. He removed his foot from Stiles’ lap and pulled his own t-shirt off over his head. It was satisfying to watch Stiles’ greedy eyes trace his chest, resting on his defined stomach muscles, and the dusting of hair that led down to his pants. 

 

“I want a back massage, pledge.” He said casually, dropping back down onto the sofa, this time on his stomach, “My shoulders in particular, I’ve been at the gym a lot this week, I need you to work out the kinks.”

 

It took Stiles a few seconds to move, finally jumping into action and moving towards the sofa.

 

“What are you waiting for?”

 

“Where.. What... “

 

“Pledge, do I have to repeat myself, because I’m sure you won’t fucking like it if I do.”

 

“No brother!” Stiles sqeaked. Moving forward and deciding to straddle Jackson’s lower back. 

 

The boy had small-ish fingers, fine enough to dig into all the little sinews of Jackson’s muscles, but strong enough to actually give some pressure. The boy seemed to be balancing on his thighs while there though, as if trying to hide his erection from Jackson. It wouldn’t do.

 

“So, pledge. Tell me what it’s like to have such a little cock.”

 

“I don’t think it’s that little, brother.”

 

Jackson does a very put upon sigh, “It’s ok, you can admit it to me. I’ve seen it. I know what your clit looks like pledge.”

 

Stiles hands didn’t stop moving on Jackson’s shoulders, but he could feel little tremors of strain jittering through the boy’s calves that ran parallel to Jackson’s body. 

 

“Did you like flicking your clit for me yesterday?”

 

“No-no brother.”

 

“I don’t think that’s true pledge, I saw you cream your panties, tell me the truth. Tell me how good it felt to pinch your little clit”

 

“Ok… I liked rubbing my clit for you brother. It felt good to have you tell me what to do.”

 

Stiles’ hands had finally stopped moving, and his waving legs meant that his body was dipping low enough that Jackson could just about feel the pressure of the boy’s dick press against his spine. 

 

Like before, Jackson suddenly couldn’t bear not being able to see Stiles’ facial expression. Leaping up so suddenly that Stiles screamed a little when as he fell onto the couch proper, before Jackson straddled the boy’s hips, reversing their previous position but with Stiles’ facing up at him. .

 

Stiles squawked a bit until he felt Jackson brush their cocks together, Jackson’s erection was clothed but still pressing against the other boy quite obviously.  Stiles looked up at him with wide eyes, pouty mouth parted in a forgotten protest.  He whined a little when Jackson rolled his hips, grinding them together.  

 

“You feel that?” Jackson hissed, nose hovering just above Stiles’.  “That’s what a man’s cock feels like... can you feel it pledge?  How hard it is against your baby cock?”

 

Stiles was panting now, short little gusts that warmed Jackson’s lips.  He almost squeaked when Jackson reached down with one hand and undid his jeans, pushed them down just enough so his hard cock could tent out his boxer briefs.  Jackson circled his hips, rubbing them together, and fought back a groan at how good Stiles’ felt beneath him, cock chubbed up but still soft, still with some give to it.  He thrust against Stiles, just to see what Stiles would do.    

 

Stiles’ eyes were closed, tight enough to wrinkle at the corners.  His mouth still hung open, chest heaving with his gasps.  Jackson took full advantage of the moment and drank in Stiles’ humiliated blush that spanned down his long throat past the dip of his clavicle and onto his chest.  Stiles had surprisingly broad shoulders but a skinny chest, lean all the way down.  He didn’t have much on him in way of fat, pecs flat unlike Jackson’s own sculpted ones.  Stiles’ nipples though were a little wide, the buds already a bit puffy where they stuck out.  Jackson dragged a palm up the side of Stiles’ chest, greedy fingers rubbing over the tightening nubs, pinching them until they grew tender and rosy with blood.  Stiles whimpered, back arching against the hurt, inadvertently pressing himself up into Jackson.  

 

Jackson couldn’t stop rolling the other boy’s nipple between his fingers, wanted to feel it between his teeth, to taste the salt of the flesh there.  “You want me to suck on your little titties, Pledge?” Jackson sneered, “fatten them up like a girl’s with my mouth?”

 

Stiles squirmed beneath him, his pulse quickening and hips starting to flex of their own accord.  Jackson cruelly twisted Stiles’ nipple between his fingers until the other boy hissed in pain.  “Answer me, pledge.”

 

“I want- I want.” The boy was keening, pushing his body upwards Jackson’s hand, a deep line of concentration wrinkled across his brow, “Whatever you want brother.”

 

A smirk dragged up Jackson’s lip, his eyes were filled with violence and smug success over manipulating someone.

 

He pressed his free hand down on Stiles’ sternum, restricting the boy’s ability to control the pressure Jackson was touching him with, and moved on his mouth down to cover the nipple that had yet to be abused.

 

Stiles moaned as soon as his mouth touched his flesh, trying to shift up under Jackson’s hand, but failing to move the heavier boy. Jackson latched his lips around the dusky nipple, and  _ sucked _ hard, the noise lewd, and clearly making a show of sucking on the boy’s tits like he was a girl. In tandem he gently teased his finger over the recently abused other nipple, catching his nail against the hard nub ever so often, cupping the inflamed flesh around like it was a woman’s breast.

 

The boy beneath him whined noisily, shaking his head side to side to portray his overstimulation, and bucking his hips up in an attempt to get friction on his rapidly hardening cock.

 

With a loud pop, Jackson tore his mouth away from the wet flesh. 

 

“I should have gotten you a full set of underwear pledge. You need a little bra to keep these puffy tits hidden. Look how rosy they are, calling out to all the boys about what a little girl bitch you are.” 

 

Stiles whined even louder at the suggestion.

 

Jackson’s own erection was now calling to him however, unlike last time he didn’t think he could push off his own climax. A small threat of ‘If you let him see you cum, he’ll have that on you’ slithered through his mind, but the sight of Stiles’ wet shame-bitten lips called to him all the same.

 

In a rush, Jackson pulled out his dick and jerked it roughly a few times. Stiles eyes snapped open at his actions, the boy’s wide eyes tracked the movement of Jackson’s hand, as a quick tongue licked across his lower lip, as if subconsciously.

 

Jackson groaned, “You’re made for taking dick pledge.” shuffling his body forward, and sliding a hand around the teen’s neck to help position him. “I bet you’d look even better with my cum decorating your mouth.”

 

Jackson was jerking himself at a quick, maddening, pace now, each time he dragged his foreskin down, he pushed his dick against the wet lips in front of him. 

 

“I knew you’d look good with glossy lips.” He muttered, smearing his pre-cum messily across Stiles face. Jackson’s hips thrusting forwards unconsciously, as if knocking on the door for entry into Stiles’ mouth. 

 

Jackson felt his pulse quicken, blood pounding in his ears as he looked down at the mess his prick was drooling all over Stiles’ swollen lips.  He had Stiles by the hair before he realized it, was jerking his head back cruelly without thinking.  “Open your mouth,” he hissed, voice low and thick with his own arousal.  “Come on, pledge, open your mouth... just like that.”

 

Stiles had tentatively parted his lips, and Jackson thrust his hips forward just enough to push the head of his cock between them, leaving a gleaming bead of precum in its wake.  “Take the head in,” he urged.  “Just the head, lick it.”

 

The tip of Stiles’ tongue peeked out, flicked unsure against the crown.  Unpracticed, Jackson thought, which only made his heart beat a little faster.  He wanted his dick to be the first one in this boy’s mouth, the first one he’s touched besides his own.  After that, he was too excited to do much more than grip Stils by the hair and drag his cock along the rim of his lips, paint that petal soft skin with his spunk.  

 

Stiles shuddered, breath a warm caress. He wasn’t looking at Jackson, his eyes closed and face near tomato red. Jackson felt a shiver thrill at the power he held over the other boy, the resignation in the furrow of Stiles’ brow, but then Stiles’ tongue darted out again, unbidden.  It snaked a firm drag across the head of Jackson’s cock, dipped longingly against the slit, and Jackson had only a spare moment of shock before he came.  His mouth hung open through the aftershocks, body frozen as he watched his cum catch in Stiles’ open mouth, across his nose, on his chin.  Time felt slowed, and just as he began to come down from his high, the reality of the situation firmly took root.  

 

Jackson had pushed the limits before this, gone well over the line of what was acceptable even in the world of fraternity hazing. What he’d done though, rubbing his cock on a pledge’s mouth, on Stiles’ mouth, making Stiles suck him, cumming on his face...he had officially taken things way too far, possibly far enough that Stiles could have him expelled from the frat or even the school.  

 

With less grace than he can usually attain, Jackson shoved his softening cock back into his underwear and fastened his jeans.  He took Stiles by the hair again, yanked his head back so he could look down at Stiles, make him feel small and helpless, get the upper hand back somehow.  

 

But Stiles wasn’t trying to get away, only winced a little at the harsh pull of his hair, but otherwise kept looking up at Jackson through his dark lashes.  He drew his plump lower lip into his mouth, sucked on it a little to taste what Jackson had left there, and he moaned.  

 

“Permission to cum, brother,” Stiles mumbled, meek as a church mouse, but eyes practically blown black with want.  

 

Jackson swallowed hard, eyes a bit wild when he looked down to see the wet patch spreading across the front of Stiles’ underwear, the white fabric a little translucent where it was pushed taut by the head of Stiles’ stiff cock.  

 

Jackson felt torn between two very different, but equally strong urges. The first was to push Stiles away, call him a disgusting little faggot, and make it clear that this only happened because Stiles was begging for it… The other was to put his mouth on that little damp patch on Stiles’ underwear, feel his dick leap under the warm pressure.

 

In the end he did neither, just (a little dumbly, although he’d never admit it) gritting out a, “yessss”, and tracking the movements of Stiles hand as it jumped to his cock through his underwear. It didn’t take even a minute, one second Stiles was cupping the head of his dick, the next he was shaking, mewling in pleasure, sucking more of Jackson’s cum into his mouth, making a mess into his already sodden underwear.

 

Jackson couldn’t be certain, but he was almost sure he could hear the boy whine out his name as he threw his head back and rubbed the head of his cock and climaxed. 

 

Jackson was still just frozen there watching the creature below him pant in exhaustion.  They were both damp with exertion, and the only sound in the room was Stiles’ laboured breath until the boy opened his eyes, his mouth twitching into a soft smile as he breathing out, “did I do good for you, brother?”

 

Jackson lept off the boy like he’d been touched by fire at the words. 

 

“Get out.” He snapped.

 

“What?” Squeaked the boy, trying to get up off the sofa and follow him. Jackson pushed him back down before realising that was opposite of what he had just asked for, so instead picked up the boy’s clothes and threw them at him.

 

“Get out. Put those on. Go home.”

 

He averted his eyes from the boy’s face, already uncomfortable at the slightly crushed expression showing on the teen’s features. Everything was just suddenly a little out of control, and Jackson did not like it one fucking bit.

 

“Get out. Don’t come back until I text you.”

 

And with that, Jackson stormed from the room, heading towards the privacy of the house’s shower room, where he could lock the door, and lock what had just happened out.

  
  
  


**Notes for the Chapter:**

> As you can see, I'm updating this pretty much every week.   
> Which is the beauty of writing the majority of a fic before you start posting it (:
> 
> Kudos & comments please, we love praise! <3


	4. Night 4.

**Summary for the Chapter:**

> Jackson has to think about what he's done, and what that might mean.  
> Also, hazing is really weird. 
> 
> Warnings at end.

Jackson had turned his phone off directly after kicking Stiles out the day before. He’d secluded himself in his room with a bottle of Jamesons, and ignored the world. He hadn’t even answered when Danny had rapped on his door and tried to get him to go clubbing with him. Jackson was determined to do nothing but watch Netflix and drink himself through his uncertainty.

 

When he woke up, however, he felt like utter shit. The alcohol had left him with a miserable hangover, and all he could do was think about what had happened the night before. Jackson was fucked. For three reasons: 1, he had definitely crossed the line with the hazing. The frat had some pretty loose morals when it came to screwing over their pledges, but actually fucking their mouths wasn’t really the same as pissing in their food, or forcing them to embarrass themselves in public. Jackson was certain that if the house found out just how far he’d gone, he’d be in serious fucking trouble. 2. Jackson wasn’t the most clued in person in the world, but he’s pretty certain that when someone is forced to be “your slave” for a week… Consent for getting their mouth fucked is out the fucking window. Stiles might be legitimately pissed at him, and therefore determined to make his life a misery. In fact, Jackson would be 100% certain his life was over if it wasn’t for point 3. which was, Stiles had liked it. And that was still a problem, a serious fucking problem because Jackson wasn’t gay.

 

Really, he wasn’t. There’s a reason why he had put Stiles’ in girls underwear and outrightedly feminised him, because Jackson liked women. Not men. Hazing the pledges and messing around was one thing, but he was not letting it get out that he was into guys. His father would kill him for one, and, as well, the usual thing with people thinking you like guys, they’d think he was gay.

 

Jackson didn’t see himself as homophobic though, his best friend was gay! And in fact, seeing some of the shit that Danny had had to put up with over the years was one of the reasons Jackson knew he couldn’t be gay, because like hell would he put up with that shit.

 

All these thoughts had been running through the boy’s head when he finally switched his phone on. Five of the texts were from Stiles, various levels of “Are we ok?” “Did I do something wrong?” and “Please talk to me???”. The final text was from Derek, one of the brother’s, saying that hell week activities would start at 3pm.

 

Jackson looked at the clock and groaned, it was already 1pm, and he hadn’t even showered yet. Knowing that if he stayed in bed any longer he’d be arousing suspicion, he dragged himself up and into the shower.

 

When 3pm rolled around Jackson was feeling marginally better physically. He was now clean, fed and hydrated, and it no longer hurt whenever he heard a sound louder than a mouse. Jackson had wanted to head to the gym to work off some of the nervous energy present in his muscles, but it’d be too obvious that something had happened if he didn’t show up.

 

When he walked into the yard, however, he was not expecting to see all the pledges on their knees, topless, their dicks out, with water balloons over the heads of their cocks.

 

“What the fuck is going on?” He snapped, they looked fucking ridiculous.

 

Derek - that day’s pledge master - turned to him and said, “Just some creative ideas for penalties." He said with a sly grin, before turning to the pledges, "Alright you pieces of shit, you each have 4 litres of water in front of you, I want you to drink every last ounce of those bottles, until you’re pissing yourself, you got that?”

 

“Yes brother.” Shouted the pledges, them all grabbing that water bottles and glugging down the contents.

 

It didn’t take long until some of the boys started looking a bit uncomfortable. Jackson had been trying to ignore Stiles up until now, especially when he’d seen the boy earlier try to catch his eyes, but now he felt himself drawn to the boy. Stiles was fairly skinny, his stomach naturally flat, although normally soft due to the lack of definition. Now however, his stomach was distended generously with water, the mound pushing his flesh forward and creating a perfectly circular bump. Jackson had to restrain himself from walking up and pushing his hand up against it.

 

“Hurry the fuck up and piss yourselves! We’ve got more water to make you drink if you don’t, so just fucking get on with it,” barked Derek.

 

Jackson was still casting a critical eye at the man over his plan, but watched with avid curiosity as Stiles - clearly embarrassed from being made to piss in front of people - grew a delicious colour pink while filling the water balloon in front of him.

 

It took nearly an hour on the whole, for each of the pledges to drink enough water and piss it out so that the water balloons were sufficiently filled.

 

“At fucking last, now tie off the balloons, and leave them under that table.”

 

Derek then handed out bunches of bananas to all the brothers.

 

“You pieces of faggot shit are gonna’ learn what it’s like to be a bitch in this house. The competition works like this: whoever can deep throat a banana - held by one of your caring brothers of course - the furthest gets the rest of the day off. If you want to give up or opt out, you’re gonna get a balloon filled with piss thrown at you, and then made to walk through the quad covered in it… And you miss your chance for an evening off!”

 

Jackson’s eyebrows were pretty much in his hairline by now.

 

“All right, let’s get this shit started. Brothers, grab your pledge slave and fuck his mouth with a banana - remember - if your pledge wins, you lose your slave for the day, so don’t make it easy!”

 

Jackson picked up a banana along with his fellow brothers, but without some of their bemused enthusiasm.  The brothers all stood in a line then as directed by Pledgemaster Derek, the bananas held in one fist against their crotch.  The pledges were then arranged on their knees before them, given a moment to survey the challenge and plan their attack.  Stiles sank heavily to his knees in front of Jackson, wide eyes fixed on him even though Jackson refused to meet his gaze.  

 

“Alright pledges,” Derek said, pacing behind them.  “Get sucking, come on you pussies who wants to go home?”

 

Most of the other brothers stepped forward, pushed the banana towards their pledge, but Jackson remained still.  Stiles shuffled forwards on his knees, hands on his thighs as he leaned forward and opened his mouth.  

 

Jackson turned his head, focusing instead on the other pledges.  It didn’t affect him to see them open their mouths wide, try to take in the phallic fruit.  He didn’t feel so much as a twitch in his cock as their faces got red from trying not to cough, or going too deep.  

 

Derek stopped beside Stiles, crouching down with his hands braced against his knees.  “This pledge here knows how to take it...you like that banana in your throat?”

 

Stiles nodded, eyes a little wet from strain as he drew back on the banana, mouth sliding along the length of it as he withdrew.  “Yes, Brother.”

 

Jackson knew it was expected of pledges to be amenable and answer in the affirmative, no matter how degrading the question, but he still felt the first flutters of arousal.  He heard Stiles sniffle and looked down, watched him take in a deep breath before letting it out and taking the banana back into his mouth.  Jackson’s own breath caught when he watched Stiles’ throat bulge a little as he worked the banana in deep, ripple when he gagged.  

 

“I bet you wish that was Brother Jackson’s dick in your throat right now, don’t you pledge?” Derek barked.  

 

Jackson went hot at Stiles’ nod, at the fat tear that dripped down Stiles’ cheek from the effort of not gagging when he pushed his mouth lower on the banana, his lips almost meeting Jackson’s fingers.  

 

Jackson felt lightheaded when he imagined it was his cock between Stiles’ lips, trapped in his spasming throat.  He knew his dick was getting hard, that he wouldn’t be able to hide it for long in front of his fellow brothers, but Jackson wanted to rip that banana out of Stiles’ mouth and shove him down onto his own prick.  Knew the spit Stiles left behind on the fruit was from him wanting the same thing, mouth watering with the need of it.  

 

“That’s it baby” Jackson hissed through clenched teeth, the sound almost too low for even Stiles to hear, but Stiles moaned at it, and on the next downstroke his lips pressed against Jackson’s fingers.

 

“Ding ding ding, we have a winner!” Derek shouted to the braying delight of the other frat members.  It was enough to shake Jackson from his revery and realize that it was over for him, that Stiles would be sent home for the rest of the evening.  

 

**Notes for the Chapter:**

> Warnings:  
> [spoilers]
> 
> Mention of urine, although no actual watersports. As part of the hazing drama, the pledges are forced to piss in waterballoons.  
> There is a sexual nature to the hazing tonight, with the pledges having to deepthroat bananas, but - as always - the pledges are always free to leave and not take part.  
> So - peer pressure as a form of coercion, but no physical coercion. 
> 
> \----
> 
> This chapter is a bit short & sweet, as it inevitably becomes the set up for the next chapter.   
> Also, I (Alt) have no idea where the idea for the pissing in the balloons thing came from for the hazing. It just seemed like something frat boys would do.


	5. Night 5

**Summary for the Chapter:**

> Jackson finally begins to over come a few of his hurdles for what he wants... Although he manages to build some new ones as well.

**Notes for the Chapter:**

> Warnings at the end.

The evening before had been awful for Jackson.

 

He wasn’t sure if the boy had been trying to pay him back from ditching him the night previous, but when he called Stiles after the competition, the phone was switched off. Jackson couldn’t totally blame the boy - hell week was, well, hell - and a night of not having to do chores or  _ bend _ to someone’s whims had probably looked very enticing. That didn’t change the fact that Jackson had a hard on like a fucking brick however, and now had two very clear images of Stiles’ mouth on his dick: one on his knees in front of him, the other with him pinning the boy down. 

 

He’d spent a good hour trying to get hold of the boy, before resorting to getting out the photos from the first night of Stiles being his ‘slave’, and jerking himself off to them. Having the photographs helped, but it wasn’t really enough. 

 

The problem was that the following day, Jackson was now twice as anxious to get the boy alone, and twice as eager to begin bending the rules.

 

It didn’t help that when the boy finally turned up at the house he had a smug air to him, like he just  _ knew  _ how much Jackson had wanted to get his hands on him the night before. 

 

“Keep it cool.” Jackson reminded himself, barking off an order for Stiles to put his hamper of dirty clothes through the wash, and trying not to look at the boy. Stiles already looked a little unsure when Jackson wasn’t instantly jumping him, but that’s what the older boy wanted: he wanted to be in control, he wanted Stiles to know he was the one in control. 

 

On impulse he called Danny into the living room with him and set up a game of Fifa between them, idling a conversation between them about parties, school work and sports. He had snagged a couple cans of beer and put them out in front them, but they mostly nursed the drinks. Jackson had known Danny for years, and the boy was one of the few people that Jackson truly felt comfortable around. It probably helped that Danny knew everything about him already: that he was adopted; his not-so-healthy relationship with drinking a few years back… It also helped that Danny was gay. So whenever Jackson had some of his  _ less than heterosexual  _ thoughts, at least he knew Danny wasn’t judging him.

 

During their game playing Stiles had finished his job and returned to Jackson. The older teen had sent him off on another menial task, followed by another. Each time, trying to ensure he was invested into a conversation with Danny by the time the boy returned, causing the boy to wait until Jackson had time to notice him. 

 

After the third time this happened, Danny was clearly getting wise to it. When Stiles walked up and asked a clipped “Anything else I can do for you,  _ brother _ ?” Danny placed a hand on Jackson’s thigh and began a story recalling the time the two of them had gone swimming in the sea together. Jackson watched puzzled, before ordering Stiles away again on a trip to catalog the contents on the house's fridge.

 

When they were alone again, Danny snatched his hand back and gave Jackson a grin. “Very good Jax, now go play with your little slave and stop using me to make him jealous.”

 

Jackson spluttered for a second, as if he was about to correct Danny, but the boy cut in: “Come Jax… It’s me you’re talking to here…”

 

Jackson bit his lip, glancing around as if to double check it was just the two of them there.

 

“Do you think he looked annoyed?”

 

Danny gave Jackson a fond bit sad smile, “Yeah, something like that.” before squeezing Jackson’s leg, affectionately this time, and relocating to his own room.

 

Jackson wasn’t entirely sure what to do with that information.

 

* * *

 

 

When Stiles finally returned from his most recent menial task - the boy’s eyes glancing critically a few times at where Danny had sat previously - Jackson had a low grade alcohol buzz on. If he was completely honest, he was mostly sober, but the idea of being drunk and the subsequent freedom that it entailed, was attractive enough to Jackson that he embraced the mentality.

 

He dragged the boy to his room, locking the door behind them, before situating himself on the bed. His legs still planted on the floor, and his arms behind him to prop himself up. 

 

Jackson loved to just watch the boy. Stiles was standing there, his fingers already fidgeting with the cuff of his shirt, as the boy awkwardly altered which foot he held his weight on. At one point Jackson may have been worried that his lack of plans appeared as if he wasn’t in control: but Stiles was just so gosh-darn _subby_ , that from the second he wasn’t given an order, he retreated into his owlish staring. 

 

“Did you like your tasks as a slave today pledge?” Jackson asked, finally breaking the silence, and enjoying the little jump that pulsed through the boy.

 

Stiles shook his head.

 

“Use your words.”

 

“No, brother.”

 

“You didn’t? My, I hope you’re not saying that you dislike obeying me, pledge..” He let a little bit of violence into his voice. A threat of punishment. The role made a thrum of pleasure run through him.

 

Stiles was already shaking his head.

 

“No-no, brother! I… I want to do what you ask of me.”

 

“Ah… So, it was just the  _ type _ of commands I gave you… ….What were you hoping for pledge?”

 

A nice pink blush ghosted up Stiles’ neck, and his eyes shifted briefly to Jackson’s crotch. 

 

Jackson let out a rich laugh in response. Stiles’ evident expectation emboldening him.

 

“Of course. My little bitch, you missed getting on your knees for me.”

 

Stiles didn’t answer him, but Jackson was already slowly undoing the button on his jeans.

 

“Get on your knees for me pledge. I want you to crawl here.”

 

Stiles fell to the ground so quickly that their was a loud crack at the sound of bone hitting wood. The boy didn’t appear to be harmed however, as he instantly shuffled forward.

 

When the teen was close enough, Jackson grasped the back of his head so he could press the boy’s lips to his clothed thigh. 

 

A threat of doubt filtered through Jackson’s mind: that he wasn’t actually drunk enough to forget that this was a bad idea, that he should back off. 

 

That’s until Stiles whines noisily, bucking his head into Jackson’s palm, before biting gently at the material of his jeans.

 

“Fuck.”

 

Jackson decided to just go for it.

 

“Ok, ok you little bitch, that’s it.” 

 

Stiles whined when Jackson took him by the hair and forced his face into his crotch, nose pressed against Jackson’s hardening cock.  “This what your little tantrum was about?” He hissed, pushing Stiles’ nose along his clothed shaft.  “Couldn’t stand not having my cock in your mouth... that little tease with the banana made you grouchy it wasn’t the real thing?”

 

Stiles nodded helplessly, shoulders slumped and boneless as the tension drained from him.  He practically nuzzled Jackson’s tenting jeans, opened his mouth to lave his tongue along it, wetting the denim.  

 

Jackson’s mouth went tight as he forced back a groan.  He didn’t want Stiles to know how much he affected him, how weak he was for the boy’s attentions.  These days, he was completely consumed by Stiles, thought of little but him: what he wanted to do to him, what he wanted Stiles to do to him in turn.  It angered him to feel so completely out of control, hated Stiles for making him feel so unhinged, hated the thought of being denied him even more.  

 

“I did it for you,” Stiles insisted, breath warming the wet patch in Jackson’s jeans.  “Wanted you to be proud of me... thought if I did a good job you’d…”  He trailed off, cheeks flushed dark as he hid his face against Jackson’s thigh.  

 

Jackson jerked him back hard by the hair, wanted to see the humiliation written across the other boy’s face.  “I’d what, let you suck me?”

 

The blush crept down Stiles’ neck, lips dark with want.  “Yes,” he breathed out, desperate.  

 

Jackson’s breath shuddered out involuntarily, his free hand practically flying to his zipper.  “You want it?” He ground out almost bitterly.  “Go ahead then, slut... suck it.”

 

Stiles actually licked his lips as Jackson opened his jeans and drew himself out.  He scooted forwards on his knees and gave a kittenish lick to the underside of the head.  

 

“I said suck it,” Jackson snapped.  “Don’t pretend like it’s your first time, not after your little performance with that banana.”  He swore he could see a little spark flash across Stiles’ eyes, challenge apparently accepted.  

 

Stiles ran his tongue along his lips, wetting his mouth before leaning forward and opening wide.  He licked broad along the length, getting it slick before bobbing a few times and finally taking it deep.  

 

Jackson’s breath hitched when he felt Stiles’ throat flutter around his cockhead, gripped Stiles by the back of the head and held him in place, watched the other boy’s face go red from the strain of it.  His mouth went dry at how Stiles’ eyes watered, a fat tear slipping free to slide down his cheek as he gagged around Jackson’s length.  The boy stayed a second longer even when Jackson released him, before drawing off completely; coughing and wiping at his eyes.  

 

Stiles was back on him in a second however, starved for it as he took Jackson back into his mouth, tongue flat along the vein as he slid back and forth.  

 

“When was the first time you did this?” Jackson groaned out, leaning back against his desk.  “How old were you?”

 

Stiles smirked around his cock, mouthed at the head when he drew back.  “Fifteen,” he said, brow quirking.  

 

Jackson wasn’t sure if the information pleased or angered him.  He wanted to be the first one, the only one, but he wasn’t an idiot, people just didn’t get this good at giving head from watching porn.  “Who was it?”

 

“A guy on my Lacrosse team,” Stiles said, flushing a bit under the intensity of Jackson’s gaze.  “We all called him Boyd.”

 

“Keep sucking,” Jackson said, pressing on the back of Stiles’ head to urge him back to the task at hand.  “Did you blow him in the locker rooms?”

 

Stiles moaned around him, the vibrations sending shivers through Jackson.  “In his car, actually.  Sometimes in my room before my dad came home.”  He licked up the length of Jackson’s cock, tip of his tongue gliding lazily around the slit.  “Want to know if he was bigger than you?”

 

The smutty challenge evident in the boy’s voice, had Jackson hissing with pleasure and fucking up into that wet heat a few times. It felt good, to punish the teen’s lips, in rebuke to the catty words uttered at Jackson’s expense. Jackson wanted to ruin him, wanted to pin the boy onto the bed, and just fuck his face into the mattress. Until the boy was crying, begging, for relief. Promising to never let another person him touch him again.

 

“Fuck.” Jackson whispered again, smearing a thumb through the tears that were gracing Stiles’ cheeks again. “You want to get fucked, don’t you?” Refusing to let his cock move from the boy’s mouth, Stiles had to just nod vigorously around it. Sucking on him dutifully as he did.

 

“Yeah, you’re an obvious little slut aren’t you baby. So hungry for a cock in your mouth, trying to rile me up, just so I’ll keep you here on your knees.” Stiles cheeks had gone a pleasant pink, which spread up to his ears. It satisfied the dominant part of Jackson, now that Stiles’ sass had abandoned him. The idea dawning on Jackson that Stiles  _ wanted  _ him to behave territoriality. 

 

It was an odd moment of fear and excitement to have an inch of proof that Stiles was kneeling in front of him for a reason other than the kid wanted to get into the frat. That Jackson probably wasn’t about to find out that Stiles had 'told on him' any second. With this realisation, he decided he might as well push the boat out a bit.

 

Stiles whined slightly. Bringing Jackson’s head back into the room. 

 

He snorted, “You’re like a puppy begging for attention.”

 

Not missing a beat, Stiles popped off his erection and barked in an excitable yip and a playful grin.

 

Two things happened in response to this: one, Jackson laughed at how much of a weird freak Stiles was, but he was laughing in a way that probably a bit warmer than he intended. But then two, his dick literally leapt in approval.

 

Stiles’ eyes dilated in excitement and the obvious reaction. Hesitantly he leaned forward and licked the tip of Jackson’s dick, before sticking his tongue out gently and panting.

 

Jackson had literally no idea why this had happened, but he definitely was in no mood to stop it.

 

“You like that puppy? Taste good?” He said, his voice slightly more wrecked than he had intended it to be.

 

Stiles barked again, shuffling forward so he could snuzzle and lap gently at the crook of where Jackson’s prick met his ball. He hissed at the sudden pleasure and change of texture, running a hand through Stiles' hair, tugging at the strands, to keep the boy’s attention there.

 

“Wow. Why am I not surprised that you like being treated like an animal on your knees. FUCK - yeah, keep licking -” Stiles’ hard little tongue, wet and warm, was massaging the sensitive nerves of Jackson’s balls. “I should have known that when I called you the house bitch, you wanted the dog collar to do with it.”

 

Stiles whined low at that. The noise breathy, and probably not even intended. The thrill of it had Jackson moving his dick back to Stiles lips. 

 

He traced the sticky tip along Stiles pursed mouth, marking the boy’s already filthily wet lips with his own precome, before manovering the prick head back inside the hidden depths.

 

“That’s it, keep whining for me, my little puppy. Show me how much you like having my cock in your mouth.” 

 

Jackson was suddenly very close to climaxing, egged on by Stiles’ eager noises.

 

“Yeah, you like that bitch don’t you. Fuck, you’d be happy sitting here on your knees all night. Just swallowing down my cock. That’s it - keep going puppy - keep -  _ fuck _ .” 

 

All care for Stiles' comfort went out of Jackson’s head in those last seconds. One minute the boy was giving him these little puppy moans, the next Jackson’s cock was so far down his throat that it was nothing by muffled whimpers that emitted from it.

 

It felt fantastics. “FUCK. YES, take it. Bitch,  _ take it. _ ” And then Jackson was cumming deep down Stiles’ throat.

 

The wave of pleasure seemed to last for ever. Jackson couldn’t remember the last time an orgasm had felt so good. At some point he’d obviously released Stiles enough that the boy was not longer choking around his swollen dick. And looking down, Jackson watched as the boy was dutiful licking at the now softening erection between his lips.

 

The threat of reality felt like it was knocking at Jackson’s door, and he didn’t want it to ruin the makeshift scene they had managed to conjure between them. 

 

“That’s it puppy. What good boy.” He bit out. Unsure why the praise was the first thing that came to mind. Stiles went mad for it though. Braying in response, and pushing his hot clammy forehead against Jackson’s thigh.

 

“You want to cum tonight puppy?”

 

Stiles looked up at him, eyes wet and tear streaked, and brutally earnest. Nodding, and yipping through his sex-wrecked throat.

 

Jackson’s mind ran quickly, he didn’t want to touch the boy’s cock: it felt like to much of a betrayal of who he was supposed to be. But it didn’t make sense to order the puppy-play teen to do.

 

“You know what good puppies are allowed to do? They’re allowed hump their master’s leg. Are you a good puppy?”

 

Stiles nodded, already shuffling forward, his hips nestling closer to Jackson. 

 

“I bet you are. Show me what a good puppy you are. How much you liked sucking my cock. How hard it got you.” 

 

It took Stiles literally minutes of cajoling to start rutting himself to completion. His face was red with embarrassment - especially each time Jackson cooed at him, about how desperate the teen looked humping at Jackson’s fully clothed leg - leading to the boy burrowing his face in Jackson’s thigh, and groaning into the material.

 

“You gonna’ keep barking for me?”

 

Stiles, yipped again, the noise almost completely lost, before his hips started to staccato in rhythm, and the teen came messily across his own stomach and Jackson’s leg.

 

Jackson felt as exhausted as Stiles looked. The boy was completely lax against him, panting and sweaty, his face completely hidden from view.

 

Something about the whole evening had stolen Jackson’s energy. The thought of “I need some fucking aftercare.” floated through his head, before he pushed it to the side… This wasn’t a S&M scene, this was just hazing…. Right?

 

With a laboured sigh, he pushed the boy away from him. Stiles’ expression was particularly wary, and Jackson could see the corner of his lips pointed down into a badly hidden frown.

 

Jackson sighed again, at the pure difficulty of the situation. As if even thinking about what had happened just then was too much to think about for his sex addled mind. He pushed off the bed and shrugged out his jeans and boxers, walking over to his clothes dresser, pulling his shirt off as he went.

 

From the corner of his eye he could see Stiles kneeling on the floor, his head slightly bowed, and his expression still sensitive. Something about it made Jackson feel a little ill. 

 

In a snap decision, he grabbed himself a fresh pair of boxers, and then a t-shirt and pair of jogging trousers to. He chucked the latter two items at Stiles.

 

“Put those on.” He bit out, his voice slightly less commanding than he wanted it to be, but Stiles hopped to it all the same. “Get on the bed.” He ordered, not watching the boy, and instead turning off the light and checking the door was definitely locked.

 

Something in him felt like doing a patrol of the room, as if to check the territory for interlopers. He snorted in laughter at himself. The puppy jokes had gone to his head.

 

Stiles was sitting on the bed sheets, slightly kneeling and watching Jackson earnestly. His dejected expression had finally left him - to Jackson’s relief - but he didn’t look comfortable.

 

Jackson didn’t really want to order him to do the next bit, in fact, he’d rather just ignore everything. The older teen climbed on the bed, pushing Stiles up against the wall (Jackson refused to think of it as trapping him in the bed) before getting under the covers himself.

 

“You should sleep.” Is the last thing he said, before closing his eyes, and giving off the appearance of someone falling into slumber.

 

It took a few minutes before Stiles moved, but then the boy slipped under the duvet next to him. Pausing for a second, before hesitantly putting his head on Jackson’s arm that was spread out from his body.

 

The urge to pull the slightly boy onto his chest were palpable, but Jackson decided he already had enough things he was trying to ignore, adding snuggling to the list would probably break his head.

  
And with that thought, he let himself fall asleep.

**Notes for the Chapter:**

> Spoilers/Warnings:
> 
> Drinking before sex. Puppy play introduced without the terms being organised. Jackson generally being a bit of a rough housing dick.  
> Stiles is VERY on board with all of above however. Some attempts at making the other jealous.
> 
> ===
> 
> I hope you enjoyed this entry!  
> I (alt) referred to this chapter as the *when we didn't know how to finish a scene, so alt wrote some puppy play* 
> 
> See you all again soon!


	6. Night 6

**Summary for the Chapter:**

> The boys' relationship escalates, as does their nightly hi-jinks.

**Notes for the Chapter:**

> There's a few extra warnings in this chapter, please check the end note for spoilers if you're worried.   
> \+ see new tags.

Jackson half woke up when Stiles slid out of his bed the following morning; mostly because he had trapped the boy up against the wall, his heavy legs pinning the slighter teen to the mattress. Stiles chirped out an embarrassed "Sorry." His voice a half whisper, followed with, "I have to go tell my best friend I'm not dead." Jackson's mind was clouded with sleep, and he seriously didn't want to have to engage with what was happening. So with a halfhearted pinch of the boy's bum, he let him slink away.

 

The next day though Stiles came back in the early afternoon. Hovering around the house, always just a few metres from Jackson, but never actually asking for his attention. Jackson needed to spend a few hours actually doing some university work, and he hadn't actually asked Stiles to come over and do any hell-week related tasks. So in the end, Jackson spent the afternoon sitting at his desk doing his uni work, while Stiles lay on his bed, doing his own work (which involved a lot of highlighting, humming, and fidgeting, but over all, Jackson didn't mind the company.)

 

By the time it was getting dark outside Jackson was a bit restless himself. An hour earlier he had ordered some pizza (enough for Stiles too, and although he didn't actually offer the boy any, the abundance of food quickly encouraged the boy to share the meal) - but now he was stuck in a strange transition moment he'd never experienced before. Previously he'd invite Stiles over, line up some hell-week related nonsense, and then somehow get the boy naked. Now however they'd hung out all day, like friends.. or at least peers. Snapping into their usual dynamic felt difficult.

 

Finally Jackson got up and made a decision. "I'm going to make a phone call, do a few errands and take a shower. I'll probably be back in thirty minutes or so." He paused, looking at the teen to make sure he was listening, "If you're still here... ....If you want to go home and have the night off. Do it. If you stay here, I'll take it you're ready for more hell week stuff." He nodded once, and then left the room. Wondering if Stiles would be there when he returned.

 

Jackson ended up skipping most of his intended errands, mind too abuzz with excitement for what the night could hold. He knew deep down - or maybe just desperately hoped - that Stiles would still be there, but the anticipation still tugged at him, and set his heart into a near frantic pace.

 

Much as he longed to run back to the room, Jackson also wanted to make Stiles wait. He imagined the other boy sitting on his bed with his hands in his lap, gnawing his chapped lips with his eyes fixed on the door, ready to greedily accept whatever Jackson would do to him.

 

So instead, Jackson indulged himself in a long shower, let the hot water calm him enough that he could get himself back under control. He took his time drying off after as well, used his moisturiser and trimmed his nose hair, anything to eat up a little extra time. He tied a towel about his waist, leaving his clothes in his labelled hamper before finally making his way back to his bedroom.

 

Jackson schooled his face when he entered to find Stiles sitting on his bed, the effort mounting in difficulty when he took in the boy's state of undress. Stiles sat on the edge of Jackson's bed, hands awkward in his lap and flush creeping down his long throat and pale chest, nipples invitingly puffy and pink. He sat cross legged, one leg slipping to the floor when Jackson entered the room, at the ready for his first command. Jackson stood and just stared a moment, door clicking shut behind him. Stiles got twitchy with the extended silence, flush depending as he helplessly shrugged his broad shoulders. "I...I don't have my uniform tonight...b-brother."

 

Jackson's face betrayed nothing, though inside he felt a surge of self satisfaction. "Show me what you're wearing, Pledge."

 

Stiles looked down into his lap before begrudgingly moving his hands to rest against the edge of the bed, both legs now dangling over the side so Jackson could see his white briefs with blue piping.

 

Jackson openly stared at the little strap of material clinging to the boy's crotch. The boy's erection was obvious through the stretched cloth, and as the boy fidgeted under his gaze, a damp patch began to bleed through. Stiles let out a breathy little gasp, his hands gripping at the bedcloth.

 

"I guess this will have to do. I'm very disappointed not to see you in your panties though pledge." Jackson was holding on to the knot of his towel tightly however, uncertain whether his own rising erection would dislodge his scant covering.

 

"As punishment, I want you to pinch your little tits for me." Stiles instantly doubled in his blushing, his legs shifting ever so slightly open at the threat of Jackson's words. "That's it princess, little girls need to get their nipples pinched when they've not done as they are told. DON'T touch yourself anywhere else-" Jackson headed off, as soon as Stiles dared to put his free hand on his thigh, his fingers almost able to touch his weeping erection. "Pull on your nipples... Are you thinking about me doing it to you?"

 

Stiles keened at that, slumping backwards on the bed, so he could touch his chest with both hands, "Yessss, brother."

 

Jackson nearly had to choke down a whine as he watched Stiles arch subconsciously against the bed, a helpless little writhe as he pinched those puffy buds. Stiles squirmed in humiliation at his own reactions, eyes tightly clenched and knees drawing up until his feet were perched on the edge of the bed for leverage.

 

"That's it, Pledge," Jackson encouraged, his words a raspy hush. "Keep going, get them nice and soft for me."

 

Jackson was struck suddenly with an idea, or rather with a vivid memory of their last real encounter which gave him an idea. "That guy whose dick you sucked, the one you told me about...did he play with your sweet little titties, or just fuck your mouth?"

 

Stiles moaned, hips stuttering at the question. He nodded, eyes still clenched shut. "He-he liked to bite them," he admitted. "He didn't like to touch my cock, but he sucked on my nipples."

 

Jackson grinned, knowing Stiles wouldn't see it, and quietly strode forward, leaning down to catch Stiles' peaked flesh in his mouth and drag his teeth against it. "Like this?" he asked, breath hot against the wettened flesh.

 

"Ah! Ahhh, ahhh!" Stiles screaming, his hips thrusting uselessly in the air. "Yes! Yes, please, brother." Jackson moved his mouth away, replacing with his thumb and forefinger, so he could tug on the nipples. Making the puffy little mounds bounce. "How does this feel pledge?" He asked, giving another hard squeeze, before replacing the touch with his mouth again.

 

"Ohhhh, ohh. Brother. It hurts, but-but- AH-" he squeaked, as Jackson began to suck on his tits. The little nub rubbing against Jackson's tongue, as the swollen flesh around them noisily filled Jackson's mouth.

 

"It makes me... I want to touch  _ down there _ . It aches brother, please, it aches." Jackson liked the word ache, it suited the boy's slutty little cock.

 

With a loud pop he left the boy's chest, placing one hand heavily on the boy’s stomach, pushing downwards. Stiles mewled slightly, at first just trying to calm down, before he started panting. "Why- why does that feel - oh."

 

Jackson kept pushing on the boy’s stomach, his fingers needing deeply into the flesh above the boy's groin. Each pressed made the boy's cock leap, and seep more precum into his underwear.

 

"Does that make your little cunt ache princess. I can see your sluttly little clit get wet for me, making your panties all wet." He pushed hard, stimulating the boy's prostate from the outside. In a way that was sure to be as sore as it was pleasurable.

 

"Oh! Ohhh!" Stiles was intelligible, his feet desperately trying to let him thrust forward, but his body trapped under the weight of Jackson's grip. The boy's eyes were screwed up tight, but his mouth was open, his lips slick from abuse.

 

Jackson withdrew his hand quickly, Stiles' hips desperately chasing after it with a helpless shudder. He took a moment to look at Stiles, eyes sweeping from that red panting face down the taut line of his trembling belly to the wet spot on his white briefs. "Show me your pussy, Pledge," he ordered.

 

Stiles worried his lip between his teeth, the abused skin near cherry red. He stilled, and Jackson began to wonder if he'd taken things too far when Stiles reached down with unsteady hands and began to push down his briefs. He lifted his hips just enough to push them down the swell of his ass to mid thigh, but Jackson stopped him before he could go further. "Get your knees up," he ordered.

 

Stiles did as he was told, pulling his knees up towards his chest, cheeks almost as red as his bitten lips. Jackson rolled his eyes, pressed a palm to the back of Stiles' thigh to shove his leg further against his chest and open him up, bare the secret pink hole. He wanted to groan, to drop to his knees and drag his tongue over the tight little pucker. Stiles was so smooth, hole practically a pinprick surrounded by a shell of pink skin. Stiles' legs kept getting in the way though, long limbs tangled and straining in Jackson's hold, so with an impatient huff, Jackson released Stiles.

 

"Get on your belly, Pledge," he snapped, fingers drumming against his thighs as he waited for Stiles to clumsily comply. The boy squeaked when Jackson took him by the hips and dragged him to the end of the bed, fingers clenching in the rumpled bedding when Jackson swatted him on the ass and told him to get to his knees.

 

Once he was propped up and Jackson had dragged his thighs apart, his hole was deliciously on display once more. Jackson couldn't help but press his thumb against that little pucker, rub little circles against it to test the give. "That jock," he ground out, voice like gravel. "Did you just suck his dick, or did you let him fuck you?"

 

Stiles shook his head minutely. "Just sucking never... Never anything else."

 

Stiles let out a few little mewls at Jackson's fondling, his thighs shifting as if they were unsure whether he wanted them further apart or closer together.

 

"I'm surprised your little hole has never had a fat dick in it pledge." He let two of his fingers massage across the puckered skin, dragging it open in parts, his other hand still keeping the boys arse apart. "It's such a slutty little thing, you ever had someone touch you  _ here _ ?" on his last word he let the top of his finger dip into the boy’s hot heat.

 

"OH-" Stiles responded, his muscle clamping around Jackson's fingers in surprise, "no, no one’s even seen me there- OH JACKSON, I mean brother, just-"

 

Jackson hand begun dragging about an inch of his finger in and out of the boy's hole. Massaging the flesh around it, his spare fingers sliding down to press into the tight balls tucked up into Stiles' body.

 

Stiles had a bouncy arse, soft globes protruding from his body, that Jackson squeezed viciously with each thrust of his hand. But the boy had a neat bone structure otherwise, his waist like narrow enough that Jackson's hands felt giant in comparison. It made Jackson feel powerful, like he could fold the boy up like origami: twist him into any position he wanted.

 

Jackson's hard cock strained against the rough fabric of his towel, his balls sore with the need to cum. Stiles was a trembling mess already, skin pink and lightly sheened in sweat, and Jackson had barely touched him. He couldn't even imagine the wrecked mess he would be when Jackson finally stuffed him with cock. Caught up in such fantasies, Jackson didn't even realize he'd dragged Stiles back by the hips until his towel covered erection was mashed against the cleft of Stiles' bare ass. Both boys groaned, Stiles' more of a whine and Jackson's rumbling from deep in his chest. Jackson had never gone this far with another boy, even during other sessions during Hell Week. He'd fucked plenty of girls - through the back door n’all - and had let guys blow him, but as he humped his hard-on against Stiles' firm ass he knew it wasn't going to be enough.

 

With a deft thumb, Jackson flicked up the knotted end of the towel, pushing his hips back just enough for the damp towel to fall heavy to the floor. His freed cock sprang to full attention, slapping against the underside of Stiles' ass just behind his balls. Stiles yelped at the contact, hips surging forward and head jerking to the side in an attempt to see behind him. His eyes widened when he took in Jackson's equally naked form, brows rounded in his first real display of trepidation. "Jackson...I-"

 

"Brother," Jackson corrected, his hands skimming along the backs of Stiles' thighs.

 

"B-Brother, I... I don't think I'm rea-" Stiles flushed deeply, lashes fluttering as he tried to spit the words out.

 

"You scared to take a cock in your pussy, Pledge?" Jackson asked, practically cooing in mock sympathy. His cock twitched when Stiles nodded, but after everything they'd done he didn't want to finally spook Stiles away. Not that he wanted the other boy to sense he had any sort of upper hand in their little arrangement, but Jackson wasn't  _ completely  _ heartless.

 

He gave Stiles' rump a quick slap to get the boy's attention. "Push your legs together," he said, stepping back while Stiles' cautiously complied, "face down ass up, Pledge."

 

Stiles slumped boneless back onto the bedding, his cheek against the bed and arms limp on either side. Jackson gazed down at the sight before him, hand lazy on his cock as he stroked himself.

 

He felt slightly mesmerized by what he could see. His spare hand coming up to pull those cheeks apart so he can look at the little hole again, now that it was slightly puffy and pink from his earlier ministrations.

 

"Fuck." He grits out, the curse forced from his lips without permission. With determination, he angled his cock and fed it between the barely-there gap between the boy's thighs. "Uh, keep them together." he orders, when he feels the muscles in Stiles legs tensing from the sudden pressure.

 

The boy squeaks a delicious sound when his prick presses in far enough that the head nudges against the boy’s sack. The little globes were swollen, but small, and seem dwarfed by the imposing presence of the mushroom tip of Jackson's cock.

 

He pulls back and thrusts between again harder, abusing the boy's softest parts. Stiles squeaks again, gripping the sheet between his fingers. The tight friction was gorgeous, the lack of slick meaning that his foreskin is dragged backwards with every thrust forward.

 

Jackson can tell that Stiles is still painfully aroused, by the little moans he gives every time Jackson jolts him forward. Jackson can imagine the boy's little prick brushing against the coarse fabric beneath them with every thrust. And experiments with four quick little jabs forward to test his theory.

 

"Oh! Oh brother,  _ brother _ " Stiles blabbers at him, his arse twitching, with the obvious attempt to get more contact on his neglected erection

 

"Is your little clit hard pledge?" Jackson asks, his voice far more rough that he expects.

 

"YES! Yes Brother, can I touch it? Please."

 

Stiles is moving his arm back to jerk his neglected cock, but jackson grabs it instead and pins him to the bed. "You'll wait pledge. Naughty little girls don't get to touch their clits until their brothers say so."

 

The feminization makes Stiles blush again - the attractive pink colouring flushing all the way to his ears - while Jackson uses the leverage of being completely stretched over the boy to thrust downwards with more effectiveness.

 

He can feel the tell tale feeling that he's climbing towards actually coming. His own cock becoming painfully hard, and swelling just that bit more.

 

In a snap decision he moves himself up and grips his cock, switching the angle so it's pushing up through the cleft of the boy’s arse, dipping into the indentation of the boy's hole.

 

Jackson keeps a hand on the base of his dick, holding it loosely enough that he can jerk it, while repeatedly directing his dick up against the boy's opening. Stiles keens in response, his breathing getting louder, and breathier.

 

Jackson jerks faster, his hips thrusting forward without thought. On each move forward the head of his cock is catching on the boy's rim, dragging the boy more open for him.

 

He hasn't used any lube, so the only slick is the presence of precum, making the roughness an exquisite pressure on the head of his dick. Stiles little hole kissing the slit with every thrust.

 

Stiles is moaning a stutter-shocked noise, writhing slightly in pain that the now puffy edges of his entrance is being abused. "You - you're too big it -hurts-FUCK. It needs lube, Ja-acksonn."

 

Jackson, although he doesn't want to permanently hurt Stiles, can feel himself tremble with the threat of a little pain. "Shhh, shh. You can take it. Just the tip baby, just the tip and then I'll get you all wet for me."

 

The head of his dick is almost inside now, bruising its way in with every thurst, and Jackson can hear the baser thoughts in his head say "get inside, get inside the tight little hole."

 

Stiles stutters out a whine though, one that sounds a little too close to tears, and Jackson holds himself back. He keeps the pressure of his dick against the boy’s hole, shifting minutely, but moves a hand to grasp the boy's own prick. It's gone soft under the manipulations, and Jackson's cock leaps sadistically at the pleasure of the soft smallness in his hand.

 

Jackson wraps an arm around Stiles' chest and drags the boy up against him. He noses at the skin behind Stiles' ear, nips at the length of his throat as he reaches down between the boy's legs with his free hand. Jackson splays his fingers, framing the base of Stiles' sweet cock like he would the lips of a girl's pussy. He rubbed up and down, the V of his fingers stroking along the short length of Stiles cock until the boy was gasping in his hold again, Stiles' ass tipping back as he tried to change the angle Jackson rubbed at.

 

"You like that, Pledge? Want brother to keep rubbing your baby cock like a clit until you're nice and wet for me?"

 

Stiles nodded frantically, his short length still mostly soft but beginning to plump once more. Jackson dragged the hand on Stiles' chest up to gently encircle his throat, applying just enough pressure that Stiles had to tilt his head back to clear his airway. "Gonna get you wet and slick you with it... then I'm going to try again. You want that pledge? The tip of my cock in your little boycunt? Just the tip baby, I promise... you'll love it."

 

Stiles nodded frantically, eyes shut and breath hitching. He was rocking back against Jackson, still helplessly nodding as Jackson kept rubbing him and kissing his neck. The kissing seemed a little too intimate, but once he started, Jackson found it hard to stop. The thrum of Stiles' hammering pulse beneath his teeth was addictive, the leap of the boy's Adam's apple beneath his palm every time he swallowed or dragged in a ragged gasp. Stiles' prick was weeping precum, smearing all along the lengths of Jackson's fingers. With a smirk, Jackson withdrew his hand to return his slick fingers to the boy's puffy hole. "You ready, Pledge?" he rasped in Stiles' ear.

 

“Y-yes brother," Stiles whined, eyes still clenched shut.

 

Jackson pushed Stiles back down onto the bed, hand gripping the back of Stiles' neck to hold him in place as he once more positioned himself behind the boy, rubbed the crown of his cock against that slick rim,

 

It was still a tight fit, and the precum really wasn't the same as lube. But the slippy texture of the slick did ease Stiles open - it definitely helped that the boy was more relaxed and clearly excited, his quivering little hole tensing intermittently, but opening up slowly under the pressure.

 

"That's it princess, open up for me." Jackson cooed, he pushed the thickness of his thumb inside to the knuckle, and then pulled the boy open to ease the process. "You're going to look so good dragged open by my fat dick."

 

"Brother-brother-" Stiles chanted a few times, his body altering from pulling away, and pushing back into the pressure, in a way that was more in league with nerves than that of thrusts, but Jackson appreciated the way it massages his cock all the same.

 

Jackson pulled his finger out and replaced it with the tip of his cock, thrusting a few times to get at least the girth of it inside. Stiles whined noisily again, his body tightening.

 

"Shh-shh" Jackson placated, sliding a hand under the boy and squeezes the cock he found there so it kept its hardness. "You can take it. You like this princess, having your little cock squeezed." Stiles attempted to nod, even though Jackson had a hand on his neck.

 

"I bet you do, how about your little balls. Huh, such silly little things, I bet I could pull them off with one hard tug." He threatened idly, while massaging the sac softly. Stiles keened at this, spreading his legs wider to allow more access.

 

The way the boy was relaxing let Jackson inch in a little more, finally letting the end of his cock pop through the tight flesh.

 

"Fu-uck" Jackson whined himself in pleasure, the need to cum reaching a peak. It was so tight, and the lack of lube, meant that he couldn’t get more than two inches inside, but the close heat worked for him anyway, so much so that he could feel himself going over the edge. “That’s it, that’s it, fuck, fuck, FUCK.” He shouts, cumming, waves of pleasure lapping up his cock as his cum fills the boy’s little hole and finally gives him the slick he needs to slide all the way in. 

 

His climax felt like it was lasting forever, and his hips keep snapping forward into the cushion of the boy’s arse, wringing every last bit of pleasure from his cock. His legs had gone a little bit wobbly from the power of it all, so he let himself fall down to his side - bringing the teen with him - so they’re in a spooning position. Even directly after orgasm, his still half-hard cock felt good pressed up inside the - now sopping wet - heat. 

Stiles mewls at the change of position, he was panting heavily - tears in his eyes from the shock of having a full dick inside him - but thrusting his hips in little abortive attempts to still get off.

 

“Shh-shh,” Jackson answers him, his body damp from sweat and his legs still numb, “don’t worry princess, I got you.” He gathered Stiles closer to his body, slipping one hand underneath the boy’s frame so he could grip the straining erection waiting for him, the other hand he used to grip the hip nearest to him, so he could bounce the boy back; each movement pushing the still heavy girth of Jackson’s erection against the sensitive rim of the Stiles’ entrance. 

 

Stiles is whispering his pleases, as if scared if he makes a noise Jackson will take away his chance to get off, “please, please, please, please,” it was endearing, and Jackson hides his urge to kiss the teen by nipping him on the back of his neck. Soft little bites that bring up the milky flesh cherry pink, without the threat of the bruise.

 

Jackson increases the speed of his ministrations, his thumb and forefinger pinching the head of Stiles little dick each time, and whispers back his praise. “That’s it, you can cum for me. That’s it, you look so good, you can cum, you can cum all over yourself and me. I want you to.” Stiles lost it in seconds, squeaking out Jackson’s name, and bucking his arse back into the older boy’s lap as he goes.

**Notes for the Chapter:**

> Warnings (spoilers)  
> \- although Jackson & Stiles agree to have a scene earlier that night, they haven't got an agreed safe word.   
> At one point Jackson introduces penetration without lube, which Stiles doesn't appear to want, and Jackson ignores his hesitation. The tone of this fic is that both parties are fully invested in what's happening, but sometimes that isn't clear in the actual communication.
> 
> \--------------------
> 
> This was officially our favourite scene: just the tip! We were incredibly excited to finally publish it, & hope you enjoyed it (:
> 
> Please do comment/kudos.   
> It's a great way to make authors feel valued for their work.


	7. Night 7 (part one)

**Summary for the Chapter:**

> It's the final night of hell week and Jackson reacts to this like a totally normal and well adjusted person.

**Notes for the Chapter:**

> We've both been busy, so this one took a while to finish. The end is obviously going to have a bit of drama, so we've cut it in two, and given you the first half.
> 
> Warnings (spoilers) at end.

 

Jackson has classes all morning of the following day. He doesn’t really want to leave the bed when he wakes up, as it gives him a moment to simply stare at Stiles unhindered. The teen is an ungainly sleeper. Limbs stuck under the pillow he’s resting on, mouth gracelessly agape. Not so silent snores echoing in the morning light lit room. At some point Jackson had clearly just pinned him down to stop him sprawling, and pulled a sheet over their naked bodies. 

 

Jackson wants to feel disgusted by what he’s sharing his bed with. Stiles is so entirely uncouth. Young, stupid, needy. Utterly uncool, and particularly scatty. He’s everything Jackson had never wanted to be.

 

He’s not though. Disgusted that is. In the quietness of the morning, unbidden thoughts of how he’s really starting to feel squirm unhealthily in his gut. “Shit.” Jackson breaths out in one long breath.

 

His eyes dart to the deep red marks up Stiles’ neck, Jackson had been biting him the night previous. What’s more disconcerting however, is the distinct memory of how much Jackson was kissing the teen last night. It was a line he hadn’t intended to cross. What was Jackson saying: all of this was a line he never intended to cross.

 

Hesitantly, freed from the judgement of Stiles being awake, he touches his fingers over the bruises. All the same Stiles whines in his sleep. The boy is warm and sensitive there, and Jackson’s fingers were cold from the morning air. The touch had Stiles roll over and burrow closer into Jackson’s chest.

 

Jackson’s stomach leapfrogs over itself again, and his heart races. “ _ Shit _ ”.

 

He has double econ first thing, followed by his mandatory language credit (Jackson is actually fluent in Spanish, but he doesn’t tell the instructor this). He texts Stiles about halfway through his second class.

 

“I want to find you in my bed when I get home. Make sure you’ve showered.” 

 

He gets a text back almost instantly with an eager affirmation. Jackson finds himself struggling to suppress the smile on his face when he reads it. 

 

“Shit”.

 

As Jackson jogs back to the frat house he wonders if Stiles has been able to head home and back in the time. The teen was pretty zonked when he left him, and it was only 2pm now. With their late night that didn’t stop until some time in the 5am range, it wouldn’t be surprising if Stiles had woken up when Jackson text him. Jackson himself wouldn’t have even considered leaving bed if he didn’t have classes.

 

When he slips into the room, his eyes fall on the teen. Stiles is asleep - again. He’d grabbed one of Jackson’s lacrosse jerseys, and had pulled it on at some point. It swamped him, almost like a dress. The way the boy was lying, he could just see his soft little cock resting on the boy’s thigh, the other leg dragged forward, so Jackson could almost see the boy’s hole.

 

It was a good look. One Jackson could get used to coming home to. “ _ Shit _ .”

 

Stiles wakes up when Jackson gets on the bed, flipping over onto his back, reaching out to touch Jackson, even though the older teen knocks the hands away.  His little dick has already gotten hard, and Jackson pinches its tip. “You’re such a slut pledge.” 

 

Stiles just nods, a playful smile on his lips. It makes Jackson feel lighthearted. Imaginative. 

 

“Your little dick is so needy, I’m going to give you a treat. Let you get your dick wet for once, you ever done that before pledge?”

 

Stiles squeaks out a no. Jackson can’t bring himself to regret the idea when Stiles is already flushed red, wriggling on the bed. Jackson strips off, enjoying the audience as he reveals his cut abs and toned thighs. He pulls of the baggy jersey from Stiles' slight frame. He can hear Stiles whisper “okay, okay, okay” to himself. It’s endearing, and a little pathetic. 

 

The younger teen really does have a small cock, it’s one of Jackson’s favourite things about him. So the older frat boy only bothers with a measly bit of lube for himself, before he’s sitting on Stiles’ little dick.

 

“Fuck!” Stiles jum ps up, his fingers scrabbling for purchase on Jackson’s thighs. The few inches available to Jackson barely go inside him, and he laughs at the patheticness of the penetration. Jackson’s own cock swells, plumping up in girth as well as length. Not because it feels good (he can barely feel it) but because all he can think of is how far his own fat cock goes into Stiles’ gut. 

 

"Jesus, your little baby cock can't even get in my ass, you'll never get near my prostate.” Stiles’ little erection leaps at his cruel words, “good thing you like getting dicked, so you can enjoy sex" 

 

Jackson rocks his hips a little, snorting out some more laughter as Stiles slips out again. The teen doesn’t seem to even care, his eyes scrunched up in concentration. He hips spasming as he tries to stimulate his little nub in the damp heat of Jackson’s cleft. His skinny chest is rising and falling at a rapid pace, flush bleeding down from his cheeks to his neck and chest, and Jackson finds it kinda’ adorable how much he’s freaking out.

 

In a few minutes Stiles loses it, his cut dick creaming itself as it jolts against Jackson’s arsecheek rather than inside him. He rocks a few more times, enjoying the way Stiles squeaks out his pleasure and then winces when the stimulation gets to be too much.  “Jackson... brother... hurts,” he whines, biting his lip raw but not making any attempt to push Jackson off him.  

 

Jackson smirks, sitting back enough to nudge Stiles’ thighs apart, making a space for himself between them.  He looks down at Stiles’ now soft cock, pretty pink skin flushed dark and smeared in his own cum, round little balls still pulled up tight.  He’s still gasping these short shaky breaths, eyes going almost comically wide when Jackson reaches down to take him in hand, cock and balls easily fitting in his grip.  He squeezes experimentally, delighting at the sharp inhale it provokes.  Stiles wriggles when Jackson squeezes it again, the flesh warm and soft in his hand, slick with seed.  

 

“Can you even get it up again?” Jackson asks, lips pursed as he looks down at the little handful.  He watches as Stiles’ face pinches in discomfort, wants to roll his cock and balls between his fingers until the other boy is crying, wonders which will get Stiles harder, the stimulation or the humiliation.  

 

“Let’s get to some actual fucking.”  The casual air with which he utters the words is cutting, stains Stiles’ cheeks an even darker pink as Jackson pushes his leg up, a hand behind the other boy’s trembling thigh forcing it back towards his chest, baring his tight little hole.  Jackson barely pauses to swipe some still warm cum from Stiles’ groin with a finger and smear it around the head of his cock before pushing forward in one steady unrelenting thrust.   

 

Stiles’ back bows off the bed, mouth hanging in a helpless gape as he cries out.  It’s a gorgeous sight, Stiles’ body tense and writhing as he can’t quite handle the cock in his gut after climaxing so recently. Jackson takes pity on him, leaning down to grab a bottle of lube and dripping it over his fingers. “My cock too big for you pledge? I thought a slutty thing like you could handle something like this. I guess I was wrong.” Jackson slides his hand down, rubbing slick fingers around Stiles’ hot hole. The flesh puffy from stimulation, fluttering around the thick girth penetrating him. Jackson’s cock slips in easier, thrusting in fast so there’s a slap of skin against the boy’s ass.

 

“Fuck!” Jackson shouts, as his whole dick is enclosed by Stiles’ molten heat. Stiles is mewling under him, his body squirming. Each time Jackson pushes all the way in he keens, jaw going up in distress. He puts a hand out to try and  _ push  _ Jackson back so he isn’t so deep, but Jackson’s weight buffs it away easily. He works his cock in again, grinding it as he’s fully seated. Enjoying the torn off gasps it makes Stiles emit. 

 

Jackson has the urge to kiss him. To swallow down all the noises Stiles makes, fuck him with his tongue. It’s not a welcome though, as much as the idea makes him hot, and he soothes it instead by leaning forward and biting the back of Stiles’ thigh.

 

“Ah! Ah!” Stiles keens, pulling his thigh back and thus shifting his position so Jackson’s cock slips in deeper. “Jackson!” Stiles whines. 

 

The combination of Stiles saying his name and the increased depth has Jackson whiting out a little, speeding up his thrusts so he’s jack knifing into the boy below him. “Fuck,  _ fuck _ , fuck.” 

 

He coasts a hand over Stiles’ soft dick. The little shaft fitting in his hand along with the tight balls. He squeezes it a few times, rubbing his fingers over the vulnerable tip. Stiles whines harder, toes curling. So overstimulated that his body locks down over Jackson’s cock, gripping him and adding to the pressure as Jackson ploughs him. 

 

It’s enough, Jackson fucks in a few more times. His hand on Stiles’ thigh pushing it higher, so Stiles is more open for him. Unable to push back against his final hard fucks inside.

 

“Fuck! Take it,  _ take  _ it. Gonna’ fuck my cum inside you! Fuck! Fuck!” The sound of his body snapping inside is the chorus to his orgasm. 

 

Jackson’s body is hot, damp with sweat. Less from the strain, more from the sheer  _ pleasure  _ of what he did. He rests his head on Stiles’ chest. Enjoying the sounds of Stiles laboured breathing. His cock is still half hard, and every few seconds Stiles’ body clamps down on it, the heavy weight of it still agitating him. Finally Jackson pulls out.

 

“You take cock like a champ,” he comments with a laugh. Sliding his hand up to the boy’s hole, to stop his seed from spilling out.

 

“Brother, brother, I  _ can’t. _ ”

 

It’s a perfect fantasy for Jackson, Stiles spread open underneath him. Oversensitive from cumming and being fucked. Jackson starts playing with his soft little cock: even more diminutive when it isn’t hard. Pinching the tip, and rubbing the rough pads of his fingers along the ridges. “You sore baby? Too much for you?” He pushes his fingers inside Stiles, slipping in with ease from the stretch and the cum. 

 

Stiles whines noisily, wriggling, unable to get away from the sensation. “I bet you could cum just from me fingering you.” He twists his hands around, and thrusts two of them in with quick little movements.

 

“Wait, please  _ please  _ wait.” Jackson fingers find what he was looking for. And the reaction is Stiles’ whole body tensing, his soft little cock twitching in Jackson’s other hand. 

 

Jackson loves the control, the ability to play with whatever he wants. Stiles unable to resist him or even get out a coherent sentence. He goes to town over the little spot. Bullying it with his fingers, rubbing it hard in fast little strokes, squeezing the cock and balls he’s cupping in tandem. Stiles doesn’t get hard again, his little cock never getting any fatter, but his body starts to give over to the pleasure. Finally Jackson adds a third finger to increase the stretch, his hand only fucking in and out of Stiles’ body by an inch. So he’s constantly rubbing the sensitive node raw. 

 

The boy cums from the prostate milking. The nub under Jackson’s fingers flushing and pulsing, and the tip of Stiles’ soft cock spurting a few small strips of cum. It's a gorgeous sight, Jackson thinks.

 

Jackson removes himself from Stiles’ body, grabbing some wipes from the cabinet by the bed to wipe down his cum slick fingers. Stiles doesn’t say anything, just breathing in deep breaths, eyes kinda’ glassy.

 

“Pledge? ...Stiles?” Stiles still doesn’t say anything. 

 

Jackson wipes the cloth over Stiles’ dick to remove the cum, and the boy whines but doesn’t say anything. Spacey. The words sub space comes to mind. (Jackson may have spent a lot of time looking up this kind of thing on the internet since he and Stiles started their... whatever this was) and something about it makes him happy.

 

He cleans up the boy, rearranging the limbs so they’re in a more comfortable position. Jackson really does love being in control, and being able to  _ take care  _ fulfils that in a way he didn’t expect. He rubs his hands over Stiles body, checking he isn’t too cold. Considers covering him with a blanket. 

 

“You look pretty like this pledge.” He tests, watching Stiles’ eyes for a hint of recognition. He gets none back. “Stiles, you look good in my bed.” He rearranges Stiles so he’s spooning the slighter boy. This is how he fucked him the first time, and it feels good again. Delicately he touches Stiles face, hesitating, before he brings their lips together. It’s a slightly strange kiss, he’s never not had someone kiss him back. But he enjoys it anyway, gently pushing his tongue into his bed mate’s mouth, and sucking on the lower lip.

 

He stops after a few stolen kisses, reprimanding himself at crossing lines. Lines in his own head, of his own making. This is almost over between them he reminds himself. His access to Stiles’ body will end with the end of hell week. 

 

Jackson strokes Stiles’ arm and thinks about it. It makes him bitter. ‘ _ Perhaps I should have been softer… Made the most of the last night?’  _ He pushes the thought away, anything more intimate would have be in congruent with the fact that Stiles would be just another brother after the ceremony that night. 

  
It fills Jackson’s body with dread, and something he can’t quite identify. It spoils the moment for him enough that he leaves the bed, heading to shower with a determination not to see the boy again until the party that night.

**Notes for the Chapter:**

> Warnings:  
> As always, no prior communication about the introduction of sex acts.  
> stiles has a small dick and tries/fails to fuck jackson  
> Jackson fucks Stiles while he's over sensitive, ignores resistance  
> prostate milking. sub space. Jackson kisses stiles while out of it.  
> \------
> 
> This was one of my fave sex scenes to write to date, Jackson giving Stiles a chance to top!  
> We hope you enjoyed it too.


End file.
